Authoring is still considered a bottleneck in successful Interactive Storytelling and Drama. The claim for intuitive authoring tools is high, especially for tools that allow storytellers and artists to define dynamic content that can be run with an AI-based story engine. We explored two concrete authoring processes in depth, using various Interactive Storytelling prototypes, and have provided feedback from the practical steps. The result is a presentation of general issues in authoring Interactive Storytelling, rather than of particular problems with a specific system that could be overcome by ‘simply’ designing the right interface. Priorities for future developments are also outlined.